(2-methyl-1-naphthyl)perfluorocyclopentene | 1309657-46-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (2-methyl-1-naphthyl)perfluorocyclopentene
• 英文别名: 1-(Heptafluoro-1-cyclopentenyl)-2-methylnaphthalene；1-(2,3,3,4,4,5,5-heptafluorocyclopenten-1-yl)-2-methylnaphthalene
• CAS: 1309657-46-2
• 化学式: C₁₆H₉F₇
• 分子量: 334.236
• InChiKey: UJADWLAZRGVKPE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-(4-溴-5-甲基-2-噻吩基)-1,3-二噁烷 、 (2-methyl-1-naphthyl)perfluorocyclopentene 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.5h， 以51%的产率得到
  参考文献：
  名称：

  取代基对具有萘部分的光致变色杂二芳烃的性质的影响。

  摘要：

  合成了四个同时​​带有萘和噻吩基团的新的不对称光致变色二硫杂环丁烷，并通过单晶X射线衍射分析确定了两个二硫杂环丁烷的结构。萘环作为芳基部分直接连接到中央全氟环戊烯环上，并且可以参与光异构化反应。在溶液和聚（甲基丙烯酸甲酯）膜中，所有的二芳烃均表现出良好的光致变色性，并起着荧光开关的作用。吸电子取代基显着地将吸收最大值移至更长的波长，并明显抑制了环回复量子产率，而供电子取代基提高了具有萘部分的二芳烃的荧光量子产率。此外，循环伏安图表明，开环异构体的氧化起点和带隙比闭环异构体的氧化起点和带隙大得多。结果表明，噻吩环5-位的取代基可以有效地调节其光学和电化学行为。

  DOI：

  10.1016/j.saa.2014.09.022
• 作为产物：
  描述：

  全氟环戊烯 、 1-溴-2-甲基萘 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 生成 (2-methyl-1-naphthyl)perfluorocyclopentene
  参考文献：
  名称：

  杂芳基环对带有萘部分的二芳硫醚的光致变色的影响

  摘要：

  合成了三种具有不同杂芳基的新的不对称含萘二芳基醚，以研究杂芳基对其性能的影响。三种二芳基蒽表现出独特的光致变色性，具有良好的热稳定性，这可能归因于不同的杂芳基效应。它们的环还原量子产率以2-甲基苯并呋喃<2-甲基苯并噻吩<1,2-二甲基吲哚的顺序增加，而环化量子产率显示出相反的趋势。与吲哚和苯并噻吩相比，苯并呋喃部分可以有效地将最大吸收移至较短的波长，并显着提高二芳基乙烯的环化量子产率和荧光量子产率。

  DOI：

  10.1016/j.tetlet.2013.07.094

文献信息

• The effect of the formyl group position upon asymmetric isomeric diarylethenes bearing a naphthalene moiety
  作者：Renjie Wang、Shouzhi Pu、Gang Liu、Shiqiang Cui

  DOI：10.3762/bjoc.8.114

  日期：——

  Three new isomeric asymmetric diarylethenes with a naphthyl moiety and a formyl group at the para, meta or ortho position of the terminal benzene ring were synthesized. Their photochromism, fluorescent-switch, and electrochemical properties were investigated. Among these diarylethenes, the one with a formyl group at the ortho position of benzene displayed the largest molar absorption coefficients and

  合成了三个新的异构不对称二芳基乙烯，在末端苯环的对位、间位或邻位具有萘基部分和甲酰基。研究了它们的光致变色、荧光开关和电化学性能。在这些二芳基乙烯中，苯邻位具有甲酰基的二芳基乙烯显示出最大的摩尔吸收系数和荧光量子产率。这些化合物的环化量子产率以对位<邻位<间位的顺序增加，而它们的环化量子产率以位位>对位>邻位的顺序降低。此外，所有这些二芳基乙烯在溶液和 PMMA 薄膜中都起到有效的荧光开关的作用。
• Syntheses and Photochromic Properties of Diarylethenes with a Naphthalene and a Thiophene Ring
  作者：Michinori Takeshita、Erika Mizukami、Kazuto Murakami、Yuta Wada、Yuji Matsuda

  DOI：10.1002/ejoc.201301677

  日期：2014.6

  Two types of diarylethene, each of which contains a naphthalene and a thiophene ring, were synthesized, and their photochromic properties were studied. The photochromic properties are dependent on the bridge position of the thiophene ring. The cycloreversion of one of the closed forms of some of the diarylethenes occurred almost photon quantitatively, and the photochromic reactions were thermally irreversible

  合成了两种分别含有萘和噻吩环的二芳基乙烯，并研究了它们的光致变色性能。光致变色特性取决于噻吩环的桥位置。一些二芳基乙烯的一种封闭形式的环回复几乎是定量地发生在光子上，并且光致变色反应是热不可逆的，至少在室温下是这样。
• 非对称萘-吡咯混联型二芳基乙烯化合物及其应用
  申请人：江西科技师范大学

  公开号：CN111410624B

  公开（公告）日：2022-05-06

  本发明属于光致变色材料领域，是非对称型萘‑吡咯全氟环戊烯化合物的合成方法及其应用，所制得的两种化合物具有显著的聚集诱导发光特性。本发明提供了上述方案所述化合物的制备方法，本发明提供的制备方法步骤简单，成本低，制备条件更加温和，更加适合工业化生产，应用前景较大且针对在细胞荧光成像以及有机光致发冷光材料有较好的应用效果。
• Synthesis and photochromism of isomeric unsymmetrical diarylethenes bearing both naphthalene and thiophene moieties
  作者：Renjie Wang、Shouzhi Pu、Gang Liu、Shiqiang Cui、Weijun Liu

  DOI：10.1016/j.jphotochem.2012.06.003

  日期：2012.9

  Three new isomeric unsymmetrical diarylethenes bearing both naphthalene and thiophene moieties were synthesized. Their photochromism, fluorescence and electrochemistry properties were investigated in detail. Each of the diarylethene derivatives showed notable photochromism and functioned as an effective fluorescent switch both in solution and in PMMA films. The cyclization quantum yield and the molar absorption coefficients of both the open- and closed-ring isomers were found to decrease based on the position of the chloro substituent attached to the terminal benzene ring as follows: para- > meta- > the ortho-position. Consequently, the cycloreversion quantum yield would increase para- to meta- to ortho-chloro substitution. When compared with the unsubstituted parent compound, the presence of the chloro substituent on the terminal benzene ring of these diarylethenes, regardless of the substitution position, would considerably lower the band gaps of the open- and closed-ring isomers. Our results indicated that the chlorine atom and its substitution position have significant influence on the optical and electrochemical properties of the diarylethenes bearing a naphthalene moiety. (C) 2012 Elsevier B.V. All rights reserved.
• Photochromic diarylethenes with a naphthalene moiety: synthesis, photochromism, and substitution effects
  作者：Renjie Wang、Shouzhi Pu、Gang Liu、Bing Chen

  DOI：10.1016/j.tet.2013.04.080

  日期：2013.7

  Five unsymmetrical diarylethenes with a naphthalene moiety were synthesized, and the structures of four diarylethenes were determined by single crystal X-ray diffraction analysis. The naphthalene was connected directly to the central perfluorocyclopentene ring as an aryl moiety and available to participate in photoisomerization reaction. Their properties, such as photochromism, thermal stability, fatigue resistance, and fluorescence, were investigated systematically. All five diarylethenes, which are thermally stable, exhibit favorable photochromism, and function as notable fluorescence switches in both solution and solid media. The electron-donating substituents effectively suppressed the cycloreversion quantum yield, whereas the electron-withdrawing substituents evidently enhanced the fluorescence quantum yield of diarylethenes with a naphthalene moiety. The results indicated that the naphthalene moiety and the substituent effects played an important role during the process of photoisomerization reaction for these diarylethene derivatives. (C) 2013 Elsevier Ltd. All rights reserved.